(4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester | 753502-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester
• CAS: 753502-46-4
• 化学式: C₂₇H₄₄O₈Si
• 分子量: 524.727
• InChiKey: GCNRQFMBQCGFLG-GWQOTCSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以90%的产率得到isopropyl 3-O-benzyl-4,6-O-benzylidene-2-O,5-C-carbonyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue

  摘要：

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.009
• 作为产物：
  描述：

  碘甲烷 、 (4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以744 mg的产率得到(4aR,6R,7R,8S,8aS)-8-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-6-isopropoxy-2,2-dimethyl-tetrahydro-pyrano[3,2-d][1,3]dioxine-4a-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and acid catalyzed hydrolysis of B2,5 type conformationally constrained glucopyranosides: incorporation into a cellobiose analogue

  摘要：

  Isopropyl and p-nitrophenyl alpha- and beta-D-glucopyranosides, restrained in a conformation close to B-2,B-5 via an oxymethylene bridge have been synthesized. These four glucopyranosides were found to be hydrolyzed at similar rates, close to those observed for the parent unconstrained glucosides. In such derivatives, either alpha or beta, the exocyclic cleaved bond is synperiplanar to an endocyclic oxygen lone pair. This conformationally locked glucopyranosyl moiety was also incorporated into a disaccharide, affording a conformationally restrained cellobiose analogue which was assayed against various glycosidases. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.06.009